Sex stories

Sex stories




Helping Jess Pt. 01

Jess and I were co-workers. I always thought she was pretty hot, and I thought a few times that she made quite a lot of eye contact with me. She had a great body with long blond hair – that she normally kept in a pony tail and no fat that I could see. She had a mischievous smile, as well as a naughty sense of humour. I thought about making a move on her occasionally, but I was a bit nervous about how it would work out with us working together. I also suspected she was a class above me, and would probably say no. So I kept my distance and tried looking for love elsewhere.

We were put into the same project team, and got to know each other quite well. It was a stressful project, tensions sometimes ran high. Once or twice I felt that Jess made some mistakes, but I defended her. I think she did the same for me, she was complimentary about my skills. There were 6 in the teams, and it meant working some late nights. Often the team would go out to the pub afterwards and we got to know each other really well and liked each others' company. Sometimes the group were invited to each others house for parties.

We talked some times – and got to know each other quite well, we had some common interests with triathlon and sports. She used to play handball quite seriously, I just liked to work out myself, and occasionally swim, cycle and run. We also said we should race each other. Against most girls I would feel confident of winning, not with Jess.

As long as I managed to forget how attractive I found her, I could talk to her quite well. We found ourselves talking about anything and sharing the problems we had. Eventually the project ended, and we saw a bit less of each other. One day she called me up and asked if we could meet up, to go for lunch, she needed to talk to me about something private. I didn't think anything of it, we had met up for lunch many times, though not just the two of us.

We met up and were in the pub, ordered our food and when it came we took our food and drinks to an alcove with round tables. We soon got talking like old times, however I felt she seemed a bit nervous. After a while I asked her what she had wanted to meet me about. She went quiet, after a while she spoke 'John, this is really awkward and I am really embarrassed to be getting into this conversation.'

She paused before continuing on, 'can you keep a secret? Let me ask you something, and you can say no, but please don't tell anyone I asked you this.'

I was intrigued now, I had never seen her act this way. 'Jess, no worries, you can rely on me, I promise I will not tell anyone.'

She seemed a bit reassured, and reached out and held my hand. This physical contact was a surprise to me, we hadn't touched before, and it reminded me how beautiful she was.

'Thanks John, I knew I could rely on you. This still may be a bit of a shock to you.'

She took a drink and then started again.

'Let me say it slowly. I have a really close friend who I have promised to look after and to help her wherever I can. I feel I owe her as I have let her down in the past. She has now got a very promising academic career.'

She stopped and took her hand away and took another drink. She then took my hand again and she moved closer to me. I began to notice how beautiful she was and she was wearing a short skirt which showed off her legs that looked perfect in their nylons.

She looked me in the eyes, 'Thanks John, I am still really embarrassed about this, and I hope you don't get upset about me asking this and you can say no, and I hope you don't hold it against me.'

'Jess, come on, you know we are good friends, I would do anything for you.'

She looked at me in a funny way.

'Thanks for being nice to me John. Well my friend works in an advanced psychology area, normally cognitive, but she also works on how sexual instincts can conflict with cognitive functions. She normally works on animals, but now is moving into a new area, and is doing some basic studies on humans. Oh I am so embarrassed I am talking to you about this.'

I tried to reassure her, looked her in the eye, 'Look Jess, just say it, I promise not to tell anyone, and I promise I'll help however I can.'

She smiled at me and grabbed my hand with both her hands and moved to sit right next to me rubbing her body against mine. After a while, her hand rested on my knee. I was not sure if she was doing it deliberately, but I was having trouble thinking straight, and I certainly wasn't going to stop her.

'You are so nice John, thanks for helping making this easier, it will still be a shock I fear. Anyway, my friend is doing some studies, normally these studies are done on university undergraduates, and she has got some, but she needs more and she cannot find any more. She asked me to help. 'She is looking at the effects on people when they are unable to have sexual pleasure for a period of time.'

'OK, it's a bit unusual, but that doesn't sound too hard. You mean not to have an orgasm for some time?'

She squeezed my hand again.

'Yes, it is to go without an orgasm for 2 weeks and to keep a diary of how it feels, how it affects emotional state, decisions, physical well-being etc. twice a week there would be a detailed interview where she can ask questions. Honesty would be needed, but there is total confidentiality.'

'And you are wondering whether I could help in this?'

She looked at me with pleading eyes, 'well yes if you could it would really mean a lot to me.'

She rubbed my arm and smiled shyly at me. I noticed that her hair was loose, no pony tail and it just added to her attractiveness. I wondered to myself how I had never tried to ask her out. I was being the typical male and wanting to please this gorgeous girl, no matter the consequences.

'Well, it's not as if I have a girlfriend or anything, so yes I think I can help.'

'Oh thank you John, you have made me so happy.' She gave me a hug.

'Though, there is something I should say before we finalize this. This will be a bit embarrassing, so please don't say anything for a while. We know that the average male masturbates once a day, and even if they promise they won't, they will probably masturbate. So there is a requirement to wear a chastity belt. This would be checked by my friend or a male assistant. Is that ok with you?'

Now this was a bit of a shock, I did masturbate every day, and having that taken away would be a bit of a shock. However doing something for Jess would be great, and she was looking sexier and sexier, the longer she held my hand. I have always had some submissive thoughts, but resigned myself to not finding a suitable girl. Regardless, full chastity might be a shock.

This whole situation was really very unusual, but I thought maybe I could use it to my advantage.

'OK, I'll do it Jess, but I'd now like to ask you one thing in return. Now this might seem a bit cheeky, and you can say no if you like, though I hope you don't. And please don't tell anyone I asked you.'

'Thank you John, thank you, thank you. Please ask me.'

'OK, I'll wear the chastity belt and go through the experiment, but at the end can I take you out for dinner?'

She looked at me and beamed at me. 'Yes, I'd love to John, I thought you'd never ask.' She gave me a big kiss me on the lips.

'I'd love to go for dinner with you, and if we weren't in a pub where our colleagues might see us, I'd give you a proper deep kiss now.'

Superb! I thought, and it probably showed with my smile.

'My friend is under a bit of time pressure, and you know I travel late tomorrow night and am only back Friday night. Would you have time tonight to come over. I have been told that it is best to try it for a day first to practice, before trying it for a longer period of time. I can let you out tomorrow evening before I go, and then you have a little break. Then on the weekend we put it on for 2 weeks? Would that be ok?'

'Yes, that is fine. How should we do it – where should I go?'

'Well I suggest you come over to mine, my friend has given me the chastity belt already, and we can try it on.'

'Another thing John, do you think we could do the date tonight? I don't want to waste time, and I would like to get you into my claws as soon as possible. In fact I like the idea of you taking me out for dinner when you are locked up – I know my honour won't be compromised!' she smiled at this.

'OK Jess, then I'll see you this evening. Is 7pm ok?'

'Yes, 7pm is good – come to mine then. Can you book the restaurant for 8pm. Let's go 50:50 on the bill – you have no choice here, and please make it a very expensive restaurant, I want to see you looking your best in a suit, and I will wear one of my best dresses.'

We agreed and then chatted for a bit longer, moving on to work.

That afternoon was very hard to concentrate. I was thinking about the evening, and what I had got myself into. However the thought of going on a date with Jess made me determined to handle what was coming.

I left as soon as I could after 5pm, and drove home quickly. I ironed a good shirt, pulled out my best suit and shaved. I applied some after shave, and tried to look my best.

I thought about the situation I was getting into, a beautiful girl about to put me into chastity. This could be something I would regret, but I knew if I didn't take the chance to get to know Jess better, I would probably regret that more.

I arranged the restaurant reservation – the best one I knew. The car was a real mess, not the best way to impress a girl, so I tidied what I could, and realized I had to leave so as not to be late.

I got there a few minutes early and rang the doorbell. Jess opened the door and invited me in. She was in a dressing gown with wet hair, I guess she had just got out of the shower. She led me into the living room.

'Would you like a drink of anything?'

I asked for a water. She went and brought it back.

'I suggest we put the belt on now and get that out of the way.'

I agreed.

'OK, so please take off your trousers and underpants.'

I did so feeling quite self conscious, we weren't in a relationship yet, and here I was taking off my clothes. To my embarrassment, I was getting aroused and my penis started rising.

'Oh, someone seems happy to see me.'

I was quite embarrassed, I didn't say anything.

She took the belt and tried to fit the cage on to my penis. I realized it was a curve – I had used one before.

'I'm afraid you need to wait Jess, it won't go on while I am getting hard.'

'OK, how can we get it softer?'

'It takes time. It is hard because you are attractive. You probably need to leave the room. If you like I can put the cage on while you are out.'

'No I like the idea of doing it myself. Then stay here, I'll leave and do what you have to do to get softer.'

She left me standing there. With time I relaxed and my penis softened.

She came back in after about 15 minutes, She was still wearing the dressing gown, but her hair was drier. I hoped that she would wear something more attractive for dinner.

She managed to get the cage on. I had to help talk her through different stages, though when I moved my hands to do some parts she slapped them away. 'No, I want to do this myself, I like the idea that later I can think that I locked you away, and you had no choice.'

Of course that affected me, and my penis tried to grow, but couldn't.

'Oh, I see you like that idea. Being locked up by a girl. You seem quite unable to control your penis John, it's a good thing I am locking it up.'

Eventually she got it all ready, she lined up the lock and told me to look her in the eyes. I did so and she stared back at me and talked.

'Thanks John, I have to say I really like the idea of locking you up, and now I am going to close this lock. You are mine now.'

The lock clicked shut. Probably it was a small sound, but it sounded huge to me. The tested the key, the lock opened and then she shut it again.

Then she stood up and shook her hair.

'Would you mind if I kiss you now?'

'No, I'd love it.'

She moved close and gave me a deep kiss. It was wonderful, her hands were going everywhere, and she slipped them down my trousers and cupped my balls.

'Are you comfortable dear?' she asked me teasingly.

'Well I love kissing you, but it is a bit frustrating.'

'I have to say John, I love this power, it really turns me on. You now depend on me for any sexual satisfaction. I hope that doesn't make me cruel and that you don't mind.'

'No Jess, actually I quite like it.'

'OK, good, then let me take off this dressing gown, and we can continue.. By the way you have to stroke me all over.'

She shrugged off her dressing gown and I saw she was wearing a blue silk basque with stockings. She was stunning. I couldn't keep my hands off her. Though at the same time it was incredibly frustrating with the chastity belt.

After a while, she pulled back.

'I need to get ready and do my makeup. Let me take these keys with me.' And she left. I turned on the tv.

After about a half hour, she came downstairs, she was wearing a petite black dress, that really showed off her figure, her blond hair loose over her shoulders. She had put some make-up and looked even more stunning.

'What colour lipstick would you like me to wear dear?' she asked, she showed me a red and a pink. I chose the red.

'I thought you'd choose that. Imagine what my red lips would look like around your cock!'

I was a bit shocked at that, she was very forward.

'Oh I forgot, that won't happen, with you all locked up.' She giggled at that.

'Or maybe I should give you a blow job in your chastity belt, I wonder what noises you would make. I hope you don't mind me fucking with your mind,' she said taking hold of my arm.

'No, its fine, it just grabs me inside. I like it.'

She quickly applied her lipstick, and then we were off.Jess and I were co-workers. I always thought she was pretty hot, and I thought a few times that she made quite a lot of eye contact with me. She had a great body with long blond hair – that she normally kept in a pony tail and no fat that I could see. She had a mischievous smile, as well as a naughty sense of humour. I thought about making a move on her occasionally, but I was a bit nervous about how it would work out with us working together. I also suspected she was a class above me, and would probably say no. So I kept my distance and tried looking for love elsewhere.

We were put into the same project team, and got to know each other quite well. It was a stressful project, tensions sometimes ran high. Once or twice I felt that Jess made some mistakes, but I defended her. I think she did the same for me, she was complimentary about my skills. There were 6 in the teams, and it meant working some late nights. Often the team would go out to the pub afterwards and we got to know each other really well and liked each others' company. Sometimes the group were invited to each others house for parties.

We talked some times – and got to know each other quite well, we had some common interests with triathlon and sports. She used to play handball quite seriously, I just liked to work out myself, and occasionally swim, cycle and run. We also said we should race each other. Against most girls I would feel confident of winning, not with Jess.

As long as I managed to forget how attractive I found her, I could talk to her quite well. We found ourselves talking about anything and sharing the problems we had. Eventually the project ended, and we saw a bit less of each other. One day she called me up and asked if we could meet up, to go for lunch, she needed to talk to me about something private. I didn't think anything of it, we had met up for lunch many times, though not just the two of us.

We met up and were in the pub, ordered our food and when it came we took our food and drinks to an alcove with round tables. We soon got talking like old times, however I felt she seemed a bit nervous. After a while I asked her what she had wanted to meet me about. She went quiet, after a while she spoke 'John, this is really awkward and I am really embarrassed to be getting into this conversation.'

She paused before continuing on, 'can you keep a secret? Let me ask you something, and you can say no, but please don't tell anyone I asked you this.'

I was intrigued now, I had never seen her act this way. 'Jess, no worries, you can rely on me, I promise I will not tell anyone.'

She seemed a bit reassured, and reached out and held my hand. This physical contact was a surprise to me, we hadn't touched before, and it reminded me how beautiful she was.

'Thanks John, I knew I could rely on you. This still may be a bit of a shock to you.'

She took a drink and then started again.

'Let me say it slowly. I have a really close friend who I have promised to look after and to help her wherever I can. I feel I owe her as I have let her down in the past. She has now got a very promising academic career.'

She stopped and took her hand away and took another drink. She then took my hand again and she moved closer to me. I began to notice how beautiful she was and she was wearing a short skirt which showed off her legs that looked perfect in their nylons.

She looked me in the eyes, 'Thanks John, I am still really embarrassed about this, and I hope you don't get upset about me asking this and you can say no, and I hope you don't hold it against me.'

'Jess, come on, you know we are good friends, I would do anything for you.'

She looked at me in a funny way.

'Thanks for being nice to me John. Well my friend works in an advanced psychology area, normally cognitive, but she also works on how sexual instincts can conflict with cognitive functions. She normally works on animals, but now is moving into a new area, and is doing some basic studies on humans. Oh I am so embarrassed I am talking to you about this.'

I tried to reassure her, looked her in the eye, 'Look Jess, just say it, I promise not to tell anyone, and I promise I'll help however I can.'

She smiled at me and grabbed my hand with both her hands and moved to sit right next to me rubbing her body against mine. After a while, her hand rested on my knee. I was not sure if she was doing it deliberately, but I was having trouble thinking straight, and I certainly wasn't going to stop her.

'You are so nice John, thanks for helping making this easier, it will still be a shock I fear. Anyway, my friend is doing some studies, normally these studies are done on university undergraduates, and she has got some, but she needs more and she cannot find any more. She asked me to help. 'She is looking at the effects on people when they are unable to have sexual pleasure for a period of time.'

'OK, it's a bit unusual, but that doesn't sound too hard. You mean not to have an orgasm for some time?'

She squeezed my hand again.

'Yes, it is to go without an orgasm for 2 weeks and to keep a diary of how it feels, how it affects emotional state, decisions, physical well-being etc. twice a week there would be a detailed interview where she can ask questions. Honesty would be needed, but there is total confidentiality.'

'And you are wondering whether I could help in this?'

She looked at me with pleading eyes, 'well yes if you could it would really mean a lot to me.'

She rubbed my arm and smiled shyly at me. I noticed that her hair was loose, no pony tail and it just added to her attractiveness. I wondered to myself how I had never tried to ask her out. I was being the typical male and wanting to please this gorgeous girl, no matter the consequences.

'Well, it's not as if I have a girlfriend or anything, so yes I think I can help.'

'Oh thank you John, you have made me so happy.' She gave me a hug.

'Though, there is something I should say before we finalize this. This will be a bit embarrassing, so please don't say anything for a while. We know that the average male masturbates once a day, and even if they promise they won't, they will probably masturbate. So there is a requirement to wear a chastity belt. This would be checked by my friend or a male assistant. Is that ok with you?'

Now this was a bit of a shock, I did masturbate every day, and having that taken away would be a bit of a shock. However doing something for Jess would be great, and she was looking sexier and sexier, the longer she held my hand. I have always had some submissive thoughts, but resigned myself to not finding a suitable girl. Regardless, full chastity might be a shock.

This whole situation was really very unusual, but I thought maybe I could use it to my advantage.

'OK, I'll do it Jess, but I'd now like to ask you one thing in return. Now this might seem a bit cheeky, and you can say no if you like, though I hope you don't. And please don't tell anyone I asked you.'

'Thank you John, thank you, thank you. Please ask me.'

'OK, I'll wear the chastity belt and go through the experiment, but at the end can I take you out for dinner?'

She looked at me and beamed at me. 'Yes, I'd love to John, I thought you'd never ask.' She gave me a big kiss me on the lips.

'I'd love to go for dinner with you, and if we weren't in a pub where our colleagues might see us, I'd give you a proper deep kiss now.'

Superb! I thought, and it probably showed with my smile.

'My friend is under a bit of time pressure, and you know I travel late tomorrow night and am only back Friday night. Would you have time tonight to come over. I have been told that it is best to try it for a day first to practice, before trying it for a longer period of time. I can let you out tomorrow evening before I go, and then you have a little break. Then on the weekend we put it on for 2 weeks? Would that be ok?'

'Yes, that is fine. How should we do it – where should I go?'

'Well I suggest you come over to mine, my friend has given me the chastity belt already, and we can try it on.'

'Another thing John, do you think we could do the date tonight? I don't want to waste time, and I would like to get you into my claws as soon as possible. In fact I like the idea of you taking me out for dinner when you are locked up – I know my honour won't be compromised!' she smiled at this.

'OK Jess, then I'll see you this evening. Is 7pm ok?'

'Yes, 7pm is good – come to mine then. Can you book the restaurant for 8pm. Let's go 50:50 on the bill – you have no choice here, and please make it a very expensive restaurant, I want to see you looking your best in a suit, and I will wear one of my best dresses.'

We agreed and then chatted for a bit longer, moving on to work.

That afternoon was very hard to concentrate. I was thinking about the evening, and what I had got myself into. However the thought of going on a date with Jess made me determined to handle what was coming.

I left as soon as I could after 5pm, and drove home quickly. I ironed a good shirt, pulled out my best suit and shaved. I applied some after shave, and tried to look my best.

I thought about the situation I was getting into, a beautiful girl about to put me into chastity. This could be something I would regret, but I knew if I didn't take the chance to get to know Jess better, I would probably regret that more.

I arranged the restaurant reservation – the best one I knew. The car was a real mess, not the best way to impress a girl, so I tidied what I could, and realized I had to leave so as not to be late.

I got there a few minutes early and rang the doorbell. Jess opened the door and invited me in. She was in a dressing gown with wet hair, I guess she had just got out of the shower. She led me into the living room.

'Would you like a drink of anything?'

I asked for a water. She went and brought it back.

'I suggest we put the belt on now and get that out of the way.'

I agreed.

'OK, so please take off your trousers and underpants.'

I did so feeling quite self conscious, we weren't in a relationship yet, and here I was taking off my clothes. To my embarrassment, I was getting aroused and my penis started rising.

'Oh, someone seems happy to see me.'

I was quite embarrassed, I didn't say anything.

She took the belt and tried to fit the cage on to my penis. I realized it was a curve – I had used one before.

'I'm afraid you need to wait Jess, it won't go on while I am getting hard.'

'OK, how can we get it softer?'

'It takes time. It is hard because you are attractive. You probably need to leave the room. If you like I can put the cage on while you are out.'

'No I like the idea of doing it myself. Then stay here, I'll leave and do what you have to do to get softer.'

She left me standing there. With time I relaxed and my penis softened.

She came back in after about 15 minutes, She was still wearing the dressing gown, but her hair was drier. I hoped that she would wear something more attractive for dinner.

She managed to get the cage on. I had to help talk her through different stages, though when I moved my hands to do some parts she slapped them away. 'No, I want to do this myself, I like the idea that later I can think that I locked you away, and you had no choice.'

Of course that affected me, and my penis tried to grow, but couldn't.

'Oh, I see you like that idea. Being locked up by a girl. You seem quite unable to control your penis John, it's a good thing I am locking it up.'

Eventually she got it all ready, she lined up the lock and told me to look her in the eyes. I did so and she stared back at me and talked.

'Thanks John, I have to say I really like the idea of locking you up, and now I am going to close this lock. You are mine now.'

The lock clicked shut. Probably it was a small sound, but it sounded huge to me. The tested the key, the lock opened and then she shut it again.

Then she stood up and shook her hair.

'Would you mind if I kiss you now?'

'No, I'd love it.'

She moved close and gave me a deep kiss. It was wonderful, her hands were going everywhere, and she slipped them down my trousers and cupped my balls.

'Are you comfortable dear?' she asked me teasingly.

'Well I love kissing you, but it is a bit frustrating.'

'I have to say John, I love this power, it really turns me on. You now depend on me for any sexual satisfaction. I hope that doesn't make me cruel and that you don't mind.'

'No Jess, actually I quite like it.'

'OK, good, then let me take off this dressing gown, and we can continue.. By the way you have to stroke me all over.'

She shrugged off her dressing gown and I saw she was wearing a blue silk basque with stockings. She was stunning. I couldn't keep my hands off her. Though at the same time it was incredibly frustrating with the chastity belt.

After a while, she pulled back.

'I need to get ready and do my makeup. Let me take these keys with me.' And she left. I turned on the tv.

After about a half hour, she came downstairs, she was wearing a petite black dress, that really showed off her figure, her blond hair loose over her shoulders. She had put some make-up and looked even more stunning.

'What colour lipstick would you like me to wear dear?' she asked, she showed me a red and a pink. I chose the red.

'I thought you'd choose that. Imagine what my red lips would look like around your cock!'

I was a bit shocked at that, she was very forward.

'Oh I forgot, that won't happen, with you all locked up.' She giggled at that.

'Or maybe I should give you a blow job in your chastity belt, I wonder what noises you would make. I hope you don't mind me fucking with your mind,' she said taking hold of my arm.

'No, its fine, it just grabs me inside. I like it.'

She quickly applied her lipstick, and then we were off.

helping   jess  

Feb 3, 2018 in bdsm

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